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Column: Boston Mythology Goes on Trial Alongside Whitey Bulger

You know something is a big deal in Boston when it steals headlines from allegations that the New England Patriots’ only healthy tight end committed multiple murders.

But the trial of James “Whitey” Bulger is, if you can believe it, bigger than sports. It’s bigger than the pending trial of accused Boston Marathon bomber Dzhokhar Tsarnaev. Bulger’s trial isn’t just a fascinating, sordid tale. It’s a true-life Sophoclean drama, enacted in a Bahston accent. And, most poignantly, it’s a requiem for a city that no longer exists.

The place to start is with the jaw-dropping story that makes the plot of a Dennis Lehane thriller seem vaguely dull and predictable. The 83-year-old Bulger is standing trial on 19 murder charges, all of which he allegedly committed before 1994, when he disappeared until his 2011 arrest in California. And, in case you hadn’t heard, Bulger wasn’t just any South Boston Irish mafioso specializing in hijacking, extortion and cocaine. His brother Billy was for many years president of the Massachusetts Senate; he was widely considered the most powerful politician in the state, outstripping a series of governors, including former presidential candidate Michael Dukakis.

Each of the two famous Bulger brothers represented one aspect of Boston’s colorful Irish-American history. The pol was the last in a long line of effective, ruthless and, in some cases, corrupt machine bosses going back to James Michael Curley, John “Honey Fitz” Fitzgerald (the grandfather of President John F. Kennedy) and Frank Skeffington, the fictional hero of Edwin O’Connor’s The Last Hurrah.

According to legend, such men stood up for the solidarity of the Irish Catholic community that defined Boston for a century. Struggling against the Protestant Yankees who strove to keep them in their place, they embodied democracy in its best and worst forms. Their strength came, above all else, out of Boston’s distinct neighborhoods — the defining glue of the city, urban strongholds that the nostalgic like to remember for their familial ties, their connected parishes and their mutual support.

As for Whitey, he stands for the dark underside of those same neighborhoods that today have changed through a combination of white flight, gentrification and urban diversification. Power was wielded there not just by benignly corrupt politicians, but also by gunmen with ties to the Italian Mafia, the Provisional Irish Republican Army and, eventually, the emerging drug cartels.

You’d think it would be difficult to generate nostalgia for men who blithely (allegedly) murdered their girlfriends alongside their business partners — but you’d be wrong, as popular films like Ben Affleck’s The Town vividly illustrate. In the genre of Boston-Irish gangster nostalgia, the decline of the white robbery crews becomes a potent class metaphor for the struggles of working-class Bostonians.

If the gangster-whose-brother-is-the-politician isn’t enough to explain the fascination with the case, there’s more. For decades, Whitey enjoyed a close working relationship with Federal Bureau of Investigation agents — so close, in fact, that at least one agent, John Connolly Jr., kept Bulger informed of the whereabouts of an enemy whom he later allegedly murdered. Connolly also tipped off Bulger that other agents were about to arrest him, giving Bulger enough time to escape — for 16 years. These facts came out at Connolly’s trials, where he was convicted of murder and racketeering; the FBI has since paid some $100 million to victims injured as a result of agent misconduct.

It is Bulger’s relationship to the FBI that has come to be the other symbolic center of the trial. Apparently seeking to minimize Bulger’s mythic status, federal prosecutors have sought to prove that he was a paid FBI informant at least since 1974. Rising to the bait, Bulger, through his lawyers, has insisted that it was exactly the other way around — that he paid the police to provide him with information.

This fierce debate has, of course, almost nothing to do with whether Bulger is a murderer. The federal code doesn’t matter. What matters is whether Bulger violated the Southie code — by being a rat. (The most likely truth, of course, is that he was both rat and mastermind, both user and used.)

And the real reason the trial’s participants and the public care so much is that the version of Bulger’s past that emerges dominant from the trial will shape the story of Boston’s criminal history for decades to come — maybe forever. The stakes aren’t about the conviction of an 83-year-old man, but about whether Boston’s crooks were vicious and noble or vicious and craven. This question stands in for the deeper question of what an increasingly diverse Boston — less than half of its citizens were white as of the 2010 Census — will make of its historical heritage.

The local color and the agonizing details will both keep coming. One potential witness, a victim of Bulger’s alleged extortion, dropped dead the other day — investigation pending. Testimony is coming from Bulger’s former partner, Stephen “The Rifleman” Flemmi, who has already pleaded guilty to 10 murders. At one point, Bulger shouted at a prosecution witness, “You suck,” which led to an exchange of obscenities in the courtroom.

Bostonians will enjoy watching for these tokens of local bravado. But in our hearts, we feel terror and pity for the denizens of a world that had much good and much brutality to it — for their hubris and for the damage they did in a world that’s now gone, never to return.

Noah Feldman, a law professor at Harvard University and the author of Cool War: The Future of Global Competition and The Fall and Rise of the Islamic State, is a Bloomberg View columnist.